The Molitor Family: School Memories, Baseball Games, Sunfish Sailing

Mary, Tom Jr., Mike, and Ellie Molitor at the Hubbard Woods School pumpkin carnival, 1997. (Courtesy of the Molitor family)

Originally appeared in the Fall/Winter 2021 Gazette, by Holly Marihugh

Our WHS theme this year was “Growing Up in Winnetka,” and the Molitor family embodies that theme. They joined our community in 1994, moving into a house on Scott Avenue in Hubbard Woods. All six members recall their favorite memories about the village and the reasons they’ve enjoyed living here.

Driving north on Gordon Terrace during the December holiday season about 20 years ago, neighbors and friends would spy a roof-top Santa, illuminated in a spotlight, sitting on the house where Gordon Terrace dead ends into Scott Avenue. That’s the Molitor family home, which sported a Jolly Old St. Nick every Christmas who, after 9/11, held an American flag that waved into the new year.

“When we were kids it was just fun to watch our Dad strap an 8-foot-tall stuffed Santa suit to his back and climb up onto the roof for the holiday season,” says Ellie Molitor, a 29-year-old general manager of an entertainment event venue in New York City. “I don’t think I understood how dangerous that was, but it put our house on the map. I remember that friends would start dropping off cookies at our house and beer for our Dad.”

Now imagine the opposite season, one of early summertime along Lake Michigan when maple trees leaf out and lilacs are blooming. Grade-schooler Mary Molitor can’t wait until the last school bell rings, signaling the start of an almost three-month vacation and the carnival games, rides, and treats waiting for her on the Village Green.

“One of my favorite memories about Winnetka would be the Children’s Fair,” says Mary, now a 28-year-old teacher in Chicago Public Schools. “I remember the days before school was out, and the fair was slowly being set up. I ran there after the last day of school to celebrate with a sugary snow cone and play the carnival games. Looking back at it now, it’s so heartwarming seeing all these parents and other community members coming together to celebrate the children’s successes and welcoming the summer.”

The sisters’ older brother, Tom Molitor Jr., remembers how easy it was to navigate the village as a kid. The 31-year-old is a consultant in data analytics and early in his career spent five years working in U.S. Naval Intelligence.

“I could ride my bike to Tower Road Beach in a couple of minutes,” Tom Jr. says. “Or I’d ride up and down the Green Bay Trail. There were so many different places to go, and you didn’t have to rely on your parents to drive you. As a kid, having that freedom was pretty incredible.” The Molitor mom, Sherry, a local broker for Coldwell Banker Realty, is rock solid certain that one of the main reasons she values Winnetka is the public education her children received.

“I have a unique situation because my girls are quite different,” Sherry explains. “Mary is now a Chicago Public Schools teacher, but also is dyslexic. Ellie was the opposite. She was always the youngest in her class because her birthday is at the end of August, and she finished college in three years. I was able to get a full insight into how well the teachers worked with Mary’s dyslexia as well as Ellie’s intellect. The school system was really able to adapt to those very different styles.”

Tom Jr. agrees that the quality of education he experienced at New Trier High School was extremely high.

“I spent five years in Naval Intelligence under the NSA [National Security Agency],” Tom Jr. says. “When I got out, I had a renewed understanding of the opportunities that my parents had provided for me and that I had growing up in Winnetka and attending New Trier. I tried to push myself a bit more in college and got a degree in three years from DePaul [University].”

Mike Molitor, the youngest sibling, talks about how living next door to Lake Michigan gave him an open invitation to learn sailing and swimming and to discover what lies beneath the water’s surface.

“My favorite memory was during the summers of 6th and 7th grades,” Mike says. “I was in the sailing program at the beach, and we got lessons on Sunfish boats, the real tiny ones. You learn the basics, like how to handle the boat, tie knots, and sail, and how to reorient your boat when you capsize. Sailing was so much fun.”

The 25-year-old now works in Guest Services for the Chicago Cubs, and he recalls the mystery of glimpsing history underwater during those Sunfish outings.

“We’d also sail out to that shipwreck that’s near Spruce Street,” Mike says. “You definitely could see parts of it from looking into the surface or swimming down with goggles.” (Learn more about the shipwreck on the Winnetka Historical Society’s website.)

Tom Molitor Sr. is an attorney and part of his business is in criminal defense which places him in contact with local police departments.

“The safety of living in Winnetka is a real asset,” Tom Sr. says. “I do a lot of different things in my business, and one of them is criminal defense work. I’ve also represented police personally and police unions on the North Shore. People don’t realize what a fabulous Police Department Winnetka has compared to almost any I can think of on the North Shore. These officers are just the best.”

However, Tom Sr. says that coaching baseball in Winnetka when his kids were growing up was the icing on the cake of living here. Over a dozen years, he coached teams of 1st through 7th graders in the KenilworthWinnetka Baseball Association. Even a former Illinois governor joined Tom coaching the young players.

“There were so many wonderful kids, moms, and dads,” Tom says. “I coached with some great guys that I’m still friends with today. All the Dads were there for the fun, and we had a blast doing it.”

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